Introduction Digital health programs are urgently needed to accelerate the adoption of Artificial Intelligence and Clinical Decision Support Systems (AI-CDSS) in clinical settings. However, such programs are still lacking for undergraduate medical students, and new approaches are required to prepare them for the arrival of new and unknown technologies. At University Paris Cité medical school, we designed an innovative program to develop the digital health critical thinking of undergraduate medical students that consisted of putting medical students in AI-CDSS designers’ shoes. Methods We followed the six steps of Kern’s approach for curriculum development: identification of needs, definition of objectives, design of an educational strategy, implementation, development of an assessment and design of program evaluation. Results A stand-alone and elective AI-CDSS program was implemented for fourth-year medical students. Each session was designed from an AI-CDSS designer viewpoint, with theoretical and practical teaching and brainstorming time on a project that consisted of designing an AI-CDSS in small groups. From 2021 to 2022, 15 students were enrolled: they rated the program 4.4/5, and 80% recommended it. Seventy-four percent considered that they had acquired new skills useful for clinical practice, and 66% felt more confident with technologies. The AI-CDSS program aroused great enthusiasm and strong engagement of students: 8 designed an AI-CDSS and wrote two scientific 5-page articles presented at the Medical Informatics Europe conference; 4 students were involved in a CDSS research project; 2 students asked for a hospital internship in digital health; and 1 decided to pursue PhD training. Discussion Putting students in AI-CDSS designers’ shoes seemed to be a fruitful and innovative strategy to develop digital health skills and critical thinking toward AI technologies. We expect that such programs could help future doctors work in rapidly evolving digitalized environments and position themselves as key leaders in digital health.